Antileishmanial Carbasugars from Geosmithia langdonii

J Nat Prod. 2018 Oct 26;81(10):2222-2227. doi: 10.1021/acs.jnatprod.8b00473. Epub 2018 Oct 9.

Abstract

Two new carbasugar-type metabolites, (1 S,2 R,3 R,4 R,5 R)-2,3,4-trihydroxy-5-methylcyclohexyl-2',5'-dihydroxybenzoate (1) and (1 S,2 S,3 S,4 R,5 R)-4-[(2',5'-dihydroxybenzyl)oxy]-5-methylcyclohexane-1,2,3-triol (2), were isolated from the filamentous fungus Geosmithia langdonii isolated from cotton textiles from Assiut, Egypt. The structures of 1 and 2 were elucidated based on comprehensive 1D and 2D NMR and MS data. Compounds 1 and 2 showed antileishmanial activity against Leishmania donovani with IC50 values of 100 and 57 μM, respectively. The (1 S,2 R,3 R,4 R,5 R) absolute configuration of carbasugar 1 was assigned via 2D NMR and experimental and calculated electronic circular dichroism (ECD) data. Similarly, the tentative structure of compound 2 was shown to possess a (1 S,2 S,3 S,4 R,5 R) absolute configuration via comparing its experimental ECD data and the specific rotation with 1 as well as examining the energy-minimized 3D computational models of compounds 1 and 2.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Antiparasitic Agents / pharmacology*
  • Carbasugars / chemistry
  • Carbasugars / pharmacology*
  • Circular Dichroism
  • Hypocreales / chemistry*
  • Leishmania donovani / drug effects*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Sugars / chemistry*
  • Sugars / pharmacology*

Substances

  • Antiparasitic Agents
  • Carbasugars
  • Sugars